Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,206 ($744/night)
Casa Ybel Resort
Sanibel Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
Club Wyndham Nashville
Nashville, Tennessee- Dec 25–28, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $826 ($275/night)
Club Wyndham Nashville
Nashville, Tennessee- Dec 25–28, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $415 ($138/night)
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 5 bed/5 bath, sleeps 20
- $21,825 ($3,118/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,279 ($1,611/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,990 ($1,284/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,579 ($1,083/night)
Skiers Lodge
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Dec 25, 2026 – Jan 3, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($221/night)
Villas at Disneyland Hotel
Anaheim, California- Dec 25–27, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,985 ($992/night)
Club Wyndham Flagstaff
Flagstaff, Arizona- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,129 ($876/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,038 ($720/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,274 ($1,039/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
Sheraton PGA Vacation Resort
Port St. Lucie, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,138 ($448/night)
Marriott's Playa Andaluza
Estepona, Spain- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/night)
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,848 ($407/night)
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 25–30, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $852 ($170/night)
Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Dec 25–29, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Club Mykonos Langebaan
Langebaan, South Africa, Africa- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
Eagle Point Resort
Vail, Colorado- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,963 ($423/night)
Hilton Grand Vacations at McAlpin-Ocean Plaza
Miami Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
Massanutten's Mountainside Villas
McGaheysville, Virginia- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
The Summit at Massanutten
McGaheysville, Virginia- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 4 bed/4 bath, sleeps 12
- $2,696 ($385/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,649 ($521/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,042 ($1,720/night)
Club Wyndham Sea Gardens
Pompano Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,505 ($358/night)
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,650 ($1,950/night)
Eagle's Nest Beach Resort
Marco Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Marriott's MountainSide at Park City
Park City, Utah- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,121 ($1,017/night)
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,012 ($1,716/night)
Club Wyndham Harbour Lights
San Diego, California- Dec 25–29, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,163 ($291/night)
Grand Timber Lodge
Breckenridge, Colorado- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)